Palmitoyl chloride → Diketene

HRID 2399216Notes

Reaction equation

HRID 2399216 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7](Cl)(=[O:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)CC)C.Cl.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]([CH:3]=[C:4]=[O:5])(=[O:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 8206Palmitoyl chlorideHCID 8471Triethylamine3×HCID 11130Triethylamine hydrochlorideHCID 12661Diketene

Product 2

HCID 12661DiketeneHCID 53637487HCID 53637487, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

For this example, the alkyl ketene dimer used was palmitoyl (C16) ketene dimer, a typical fatty acid ketene dimer. The ketene dimer was prepared by dissolving 27.5 grams palmitoyl chloride in 200 mL ethyl acetate in a 500 mL Erlenmeyer flask. Then, 10.1 grams triethylamine was dissolved in 50 mL ethyl acetate and placed into an addition funnel. The solution of triethylamine was dripped slowly into the stirring acid chloride solution. A white precipitate began to form almost immediately; this white precipitate was triethylamine hydrochloride. The solution was stirred for one hour after all of the triethylamine was added. The triethylamine hydrochloride was filtered out of the solution, and the filtrate, a clear, golden-yellow solution, was evaporated under reduced pressure to yield a light yellow, waxy solid, palmitoyl ketene dimer. The yield was virtually quantitative.

Workup

  1. customplaced into an addition funnel
  2. customto form almost immediately
  3. additionwas added
  4. filtrationThe triethylamine hydrochloride was filtered out of the solution
  5. customthe filtrate, a clear, golden-yellow solution, was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bbb87c473d634bf08f3ad4f5ada4cc09
Source dataset
uspto-grants-1995_09
Patent number
US05447689

Reaction notes

Loading…